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Sixteen and sex

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Unlike a lot of people who write on this site, I don't remember the first time I jacked off. I kind of think I've always done so (I remember enjoying getting naked and feeling my dick by myself and with friends before I was in first grade). But I do remember some of my earliest sexual experiences with other guys. I say "guys" because one of the most indelible memories occurred when I was 16 and involved both my best friend, Greg, and a guy in his early 20s, but who at the time seemed all man. I'm currently in my late 30s, but I still jerk off remembering this event, and some of the ones that followed. Some background: I was a junior high and high school jock, and very competitive. Who had the highest GPA? (I was honor society vice president.) Who could bench the most weights? With the most reps? Who had the most yards carrying? (I was a running back.) Who ran the fastest sprints? Who had the best batting average? (I played third base.) RBIs? At home? Away? Who had the biggest biceps? The biggest dick? (Among white guys: me. Among all guys: a black kid named Rondell, then another black kid whose name I forget. Then me. The races didn't mix much at my school except in sports, but we were all friends in the locker room.) And even: who could cum the most times? The farthest? And who was the horniest? As you can see, there weren't too many parts of my life that didn't eventually get compared to someone else's parts. I'm hardly competitive at all any more, as I've learned the hard way that there are more important things than being #1, but I was young, dumb, and full of cum, as they say, and still had a lot of learning left to do. This is about a day I learned something about myself that's stayed with me ever since. The summer I was 16 I was trying to earn some spending money mowing lawns with my friend Greg. We earned enough to pay 18 year olds to buy us beer (back before they changed the age to 21) and to take a girl to a movie now and then, but between lawnmower repairs and gasoline, we really didn't make much at all. At the time of this story -- which I admit has had too much set-up already, but all this stuff is coming back to me as I remember it -- it was probably late June or early July, and we were set to start two-a-day practices for fall football the first week in August. Greg and I worked out together (and somewhat more) before that, because we had a chance our sophomore year for the varsity team, but there were no guarantees. So we were both pumped up that early 1980s summer to be the biggest fucking muscle-bound bad-asses we could be. By July we may have been looking pretty good, and there's no question we thought we were. On this particular day, we were supposed to mow the front- and backyard of a nice couple who'd warned us they'd be away for a whole month and a half, but had paid us in advance. (I think they also knew Greg's parents, so they felt pretty safe paying us up front.) We'd been mowing their place since end of May, but this was the first weekend they were away...not that we expected that to be any different. However, we saw somebody inside in the house and wondered to each other who it might be, but figured it wasn't anything very nefarious. We knew they had a son away at college, and I think Greg said that he saw him in the window and was pretty sure it was him. This assumption was confirmed for us when we moved from the frontyard to the back. As we moved our equipment through the wooden gate to the backyard, a voice said "Hey, you guys want a beer or something?" Standing in the doorway on the back patio was a man wearing only a towel around his waist. Dark blond hair on his head, but smooth everywhere else (that we could see). He was probably around 21 or 22, about six feet tall, and in great shape, physically. He wasn't completely pumped the way Greg and I were starting to look, but you could tell he spent some time every day working out: well-muscled shoulders, smooth pecs, well-defined biceps, and he had the same six-pack abs I'd been after since early spring. We must have just been staring, because he asked again: "Do you want a beer?" Greg said, "sure," and I nodded, and he went back inside and came back with three beers. I looked down at his towel when he handed me the bottle and could tell there was something going on down there. Whether he was getting hard or was just big enough to notice, I wasn't sure. But my curiosity and competitiveness were both engaged. It was really hot, and Greg and I were already working with our shirts off, so we were three shirtless (and one shorts-less) guys, standing on the back patio, having a beer. The guy asked us how long we'd been mowing his parents' yard, where we went to high school, if we had other jobs. He'd gone to our same high school a few years earlier, and played football for the same coach we were getting ready to impress to get on the varsity team. I didn't say much, but the guy was nice and kept including me in the conversation and would look over at me sometimes while he was talking to Greg. He was kind of sizing us up, but in a friendly way. He wasn't trying to impress us with how big a stud he was, though he probably could have. He said he was home from school for the summer, working as a lifeguard at his parents' country club. Greg's family belonged there, too, but Greg never went except for lunch after church on Sundays sometimes, so they'd never seen each other. After a few more questions and comments, I said, "Well, we've got more to mow here, so I'm going to start." The backyard wasn't nearly as big as the front, and had even less grass to mow because of a huge swimming pool and surrounding flagstone deck. Greg and I were almost finished with our beers anyway, so we thanked the guy and he went back inside while we finished the lawn job. But the beer and the testosterone and the sweat sheen on my buddy Greg's chest was all starting to go to my head, and I wanted to get finished and go home and jerk off. I was a three-times-a-day man then (nowadays, more like once or twice a day) and hadn't even had wank one yet that day. I knew Greg was probably feeling the same, because we jerked off together after most workout sessions in his garage. As I was turning off my mower to empty the last load, and he was walking back into the yard from taking his last garbage bag out to the curb, he caught me looking back at the house to try to get a glimpse of the guy inside. I felt kind of sheepish, but Greg just smiled and raised an eyebrow, cocking his head toward the house. I smiled and sort of shrugged, just as the guy walked back out, still only wearing a towel, carrying another beer for each of us. "You guys want to use the pool, you're welcome to," he said. "I'm going to go swimming in a bit, too." It sounded perfect: a cold beer and a swimming pool on a hot summer day, but Greg said, "That would be great, but we didn't bring our suits and our shorts are kind of grimy to be messing up your pool." "You don't have to wear a suit," the guy said. "I never do when I'm the only one here. None of the houses on either side or behind can see over that fence." Greg looked at me and I looked him. "Okay," I said. "It's hot enough today you could bring a parade through here to watch me in my birthday suit and I wouldn't care, just so long as I could swim in that pool." They laughed, and the guy went back inside while Greg and I finished filling the last bag and tying it up to take to the curb. Then we went over to the pool, looked at each other and then the house, and Greg said, "What the hell," and started taking off his shorts. I did the same, the only difference being that I wasn't wearing any underwear underneath, and when Greg saw that, we both started laughing. So we were both naked, which wasn't unusual for the two of us, we'd even worked out naked in his garage, but this time we were outside in someone's yard, which was sort of strange. I could tell I was starting to get a boner and Greg's dick (which was smaller than mine, but only by a three-quarters of an inch; I knew because we'd measured, and I came in at ten-and-a-half inches hard while he came in at just under ten) was swinging pretty full, so we both dived into the pool to cool off. "You think that guy's going to come out here?" I asked Greg, when we both went to the side of the pool to take a swig of beer. "Maybe," he said. "Why?" "I don't know. I guess I'm getting horny and wanted to beat off, but not if he's going to come out here and see." "Maybe he wouldn't care," Greg said, but I could tell he was joking. "Besides, what makes you think he couldn't see you from the family room window, anyway?" He was right, so I just decided to swim for a bit, then pull the shorts back on and head home to spank my monkey. The man in the towel came back outside with sunglasses on and a couple of other towels for us. "Thanks, man," we said, hanging on the side of the pool. "No problem. You need another brew?" But we didn't. Then the guy surprised us: he turned back to the chaise chair nearest us on the pool deck and took off his towel to lay it across the chair. He lay down on his back, and his fat dick hung between his legs. Greg and I gave a quick glance at each other, but the guy was talking about some coach who used to work at our school, and we kept up the conversation with the guy. I had so far managed to keep my dick down, but figured that pretty soon I was going to need to go inside and use their bathroom to jerk off. However, the second beer was starting to take effect, so a part of me didn't care if I got a hard-on in front of this guy. He was acting casual about the whole thing anyway, so I took my cue from him. Emboldened by beer, I decided to try the diving board, so while Greg and the guy kept talking, I climbed out of the pool and went over to the diving board. I wasn't drunk enough for it to affect my diving, but another beer and I would have been, I knew. I glanced over at the guy, but couldn't tell if, from behind his sunglasses, he was looking at me or not. But he looked like a model for some kind of invisible clothing (I hadn't seen gay porn at that point in my life), stretched out on the chair, his hands behind his head, and his dick soaking up the sun. I envied his confidence, though I knew other people often envied my own, so figured he probably wasn't that different from me, just older and more experienced. Though I was getting ready to experience something pretty amazing myself. I made a clean dive and surfaced to hear Greg laughing, and saw him backing away from the pool edge and swimming underwater to the deep end of the pool. "What's so funny?" I asked the guy, who was laughing, too. I was paranoid enough to think they were sharing some joke about me. "I told your friend you look like you're hung like a horse, and he said, 'Yeah. But you should see him with a hard-on for the full effect.'" I was stunned. Obviously, the beer had gotten to Greg, too, wrecking his inhibitions as it was crumbling mine. But I still blushed, and could feel my face turn red from embarrassment. "Oh, he's just bullshitting you," I said, but not very convincingly. My eyes were transfixed on the guy's cock, which was starting to rise. Greg resurfaced, and I punched him in the back, but he only laughed. "What the hell are you talking about my boner for, you fuckhead?" I said. I tried to grab him, but the water slowed our movements, and he was able to get free and grabbed me instead, putting me into a hold. "Aw, shut up," he said, while I fought back, but we were just playing around. "You said you wanted to jerk off, so I thought I'd break the ice a little." That one stunned me. My dick was already getting stiff from our wrestling in the water, and I could tell Greg's was too, but I couldn't believe he would say that in front of this man we barely even knew. I thought the guy would get pissed off and tell us perverts to get out of his parents' pool and no thanks for the lawn work, he'd take care of it from now on. But he just started to laugh. His cock was at full-mast now, too. "Hey, man, no problem!" he said, still laughing. "I do that all the time out here. Mi casa es su casa, amigo. Have at it." I was flabbergasted, but mostly that Greg and I had run across someone as open about jerking off as we were with each other. We were extremely cautious about talking about it around anyone else, however, so to find an older version of ourselves was definitely a new experience. "You kidding?" I asked. I'd set guys up myself just to knock them down with some kind of embarrassment in front of people, so I knew enough to be wary. "About jerking off out here, or about not caring if you do?" he said. "Both," Greg said. My heartrate was up and my dick was raging, but I looked down in the water, and Greg's was too. "Neither," the guy said. "See?" He started to jerk his dick with his right hand, holding his beer in his left. "Cool," I said, trying to sound nonchalant. "I've been needing to get off for the last two hours." Greg and this guy laughed, but he didn't stop stroking himself. He was going pretty slow at it, though, so I knew he wasn't going to let this be a fast one. I climbed out of the pool, and the guy looked down at my dick. "Wow. He was right, then," he said. "Yeah," Greg said. "He's got the biggest white dick at school." We all laughed at this, and I lay down on my back on the pool deck and started to stroke. Greg hauled his ass out of the water, and lay down a few feet from me. We were both about six feet from the guy in the chair, Greg was facing him but my head was aimed in the other direction, because I wanted to be cool about it, I guess. Though I certainly didn't mind if the guy watched me. "So have you guys done the standard 'who can shoot farthest' and 'who can stay hard the longest'" he asked us. "Yeah," I said. "I win for distance and volume, Greg wins on stamina." "Do you ever use lube?" he asked. "That usually brings me to a finish pretty quick." I thought he was talking about WD-40 or something. "Ewww, man. Gross," I said. "Clean-up must be a bitch." "What do you mean? It just comes off in the water." He tossed what I'd thought was his suntan oil over to me, and I saw that it was some sort of clear lotion. "Put it on your dick," he said. "You'll see." Wow! I was a convert to lube immediately. I'd have even used WD-40 if it felt that good. "Greg, you've got to fucking try some of this, man!" I tossed him the bottle and he, too, was amazed. The guy just laughed at us. "Man, you guys have to get out more," he said. The three of us just lay there, lazily yanking on our shafts in the summer sun, and shooting the shit, talking about pussy -- which Greg and I hadn't yet had -- and blow jobs, which I'd wanted to have with him, but never told him. "Don't you ever help each other out?" he asked. Of course we did, but what was interesting was that his choice of words was almost the same as Greg's and my cue for each other that we wanted to jerk the other off: "Do you need any help?" "Uh. Yeah," Greg said, hesitantly. "But we're not gay or anything, if that's what you're talking about." (We were, actually, but wouldn't admit that to ourselves for another decade.) "Gay, straight, whatever. It's just getting off, whether its your hand or someone else's," the guy said. "I've traded blow jobs with guys and I fuck pussy every chance I get, so I don't really care what you call it." This was pretty honest, and Greg and I were impressed and intrigued. He moved over closer to me, his head at my feet, and reached out for my dick. I loved it when I could get him to jerk me off, and was always glad to return the favor. The guy sat up a bit and watched us "help" each other, while he jerked off himself. His dick wasn't as big as either one of ours, but it was fat and stuck straight up, whereas both Greg and I had a slight curve. I was getting pretty heated up, but could also be detached enough to recognize that this was an awesome situation. I was enough of a narcissist to love looking at my own body while I jerked off, and I always got off looking at Greg's body, and here we were, two hard-bodied jocks with our big dicks jerking each other off while this stud jerked himself off watching us. "Did you say you've given a guy a blow job?" Greg asked. I wondered where he was going with that, and certainly hoped it was where I wanted him to go. "Yeah," the guy said. "A few times. I'm a horn dog, what can I say? I like to cum, I like it when other people cum, I even swallow cum. I figured my girlfriends do it, so it can't be that bad, and now I even like it." I think normally we would have acted grossed out by this, but we were past acting like a couple of toughs. The guy was so matter-of-fact about everything and, probably because he was older than we were, it seemed somehow more mature just to be casual and honest about everything. "You know what?" I said. They both said, what? "I've never even had a blow job, even from a girl. I don't even know what they're like." Greg knew this, because I knew the same about him, but I didn't know if the guy would respond to this or not. I thought maybe he would, though, and I was right. He stopped jerking off, and his stiff dick just stood there at full attention. "Can you suck yourself off? Have you ever tried?" I wasn't expecting that, but the answer was yes, I could get the head of my dick in my mouth, but even Greg didn't know that. Somehow that didn't seem the real deal, however. All I said, though, was: "Uh, I never tried it. Maybe I will sometime." I think the guy wanted to watch me suck myself off, but that wasn't what I was aiming for. So I guess he decided to oblige. "You want me to blow you?" he asked. "I'd be glad to slurp on that horse cock." As I said, Greg and I hadn't seen or read any gay porn at that point, and nothing racier than Penthouse and Hustler in straight porn, so this kind of talk just between guys was extremely new and extremely exciting. I was a few years older before I realized that I like to get off from hearing people talk about sex or reading about it (like on this site) as much or more than pictures. I didn't say anything, but got up and walked over to the guy's chair. Greg watched me, and jerked off. He was getting really turned on by this, and I wondered how far he'd go himself here. "Be gentle with me," I said to the guy, and we laughed. But the truth was I was nervous and excited, however the day was amazingly beautiful and hot, this studly guy in front of me was all about sex, and I looked damn good with my big hard dick and all the muscles I'd packed on over the spring and summer. I stood right in front of him, and he swallowed as much as he could, which was about three-quarters of my shaft. "Oh, my God!" I yelled. "Oh, man! Yeah!" I growled. This was so fucking awesome! I never knew it would feel so much different from jerking off. Greg was really going to town on his pud now, watching this man suck me off. I was feeling better than anything I'd ever felt before. I felt like I was going to cum and part of me couldn't even control it, it was so overwhelming. And part of me didn't want to end it yet. The guy was sucking up and down my shaft while he jacked himself off, and he'd lick the underside of my dickhead and my whole body would shudder. He was also running his hands across my chest and playing with my ass a little, but I was too deep into what I was feeling to pay much attention to the individual details. He pulled his mouth off my schlong and smiled. "Man, that's an awesome dick!" he said. "I can't even swallow the whole thing. And you've got big, massive balls, dude." "Greg's are even bigger. Give him a blow job, he's got to feel what this is like!" I said. Greg got up and came over to us, his dick in his hand. The guy started to blow him, too, and Greg closed his eyes and threw his head back. "Ohhhh....fuuuuuuck!" he said, really low and deep. He put his hands on top of the guy's head and I saw his big-man shoulders fall slack. "Oh, fucking A, man! This is incredible!" He was transported, too, I could tell. He opened his eyes and gave me a dazed look, shaking his head in amazement. I was standing right next to him, jerking myself off and watching my studly best friend get the full-length of his shaft worked over by the guy on the chair. Man, oh man, I wanted to be the one doing that to him! The guy stopped sucking for a moment and said, "I can't believe you guys never tried it with each other. Haven't you heard of a 69?" We had, and it was one of my biggest jerk-off fantasies, but neither one of us had ever mentioned it to the other. But Greg and I looked at each other with raised eyebrows, and just said "Yeah!" at the same time. We dropped immediately to the pool deck in the same position we'd been jerking each other off in, and took the other's dick in our mouths. Now THIS was incredible! I'd even give anything to be back there again, just once, in a 69 with my best friend at the side of a hot guy's pool. I've had great sex of this and other varieties, but this was the first time I'd sucked cock and found it was the most natural thing in the world to do. Greg didn't seem to suffer any obstacles either! "Yeah, dudes, go to it. That's so fucking hot!" the guy was saying, but I could only half hear him, my ears were roaring with the sound of my blood racing. I was very familiar with an adrenaline high, and also an alcohol high, and had even smoked a little pot once but didn't like it. And I knew from jerking off alone and with Greg that awesome testosterone high that happens during sex between men, but this was the first time I'd ever experienced it this intently, and my attention darted between what Greg was doing to my cock and what I was doing to his. The guy was standing over us now, jerking off hard. Greg and I were really going at it, and he even pulled off and slurped on my balls for a bit, moaning as I treated his dick to full tongue washing. "I think I'm gonna cum," he moaned, and started sucking on my stick again with even more passion. I was going to cum too, I could tell, but I was beyond doing anything about it. I didn't even know or care if Greg would be mad if I came in his mouth, because I couldn't stop it from happening, only he could. And with my mouth full of cock -- I, on the other hand, was eager for his spooge -- I couldn't warn him. Then we all three, at nearly the same time, had an orgasm. If you've never cum with someone (even just one other person) at the same time, it's great. I think I remember almost all the times in my life I've had sex (with men and with women) where we both climaxed at the same or nearly the same time. It's rarer than people assume, I think. I felt the first blast of Greg's load against the back of my throat, too fast to even get much of a taste. At the same time I could hear the stud standing above us let out a loud grunt and felt his cum land on the side of my torso, and then again on my chest. Greg was shooting at least three other loads in my mouth, and I couldn't even swallow it fast enough, when I blew my seed down his throat. I pulled off Greg's dick, and his last spurt went across my chin and onto my chest, where his juice mixed with the other guy's. Greg's mouth had something like a vacuum seal on my dick, it was awesome, and I don't know how much I squirted, but it was the longest lasting orgasm I think I've ever had. Wow. The guy fell back onto his chair, and Greg and I just lay there, with my hand still hanging onto his dick. We were all still hard, and the last remnants of cum were oozing from Greg's cock, probably from mine and the guy's, too. "Oh. My. God," I said. "I think I may have broken something in my head, I came so hard." Greg laughed, and said, "Man, I know I did. That was fucking incredible!" The guy said, "No kidding. You guys were amazing to watch. You were so into it, I think I could have cum just watching." I finally understood the expression I'd read in Penthouse: "totally spent." We all were, completely, but it felt great. We lay there for a few more minutes. "You've got jizz all over you, dude," Greg said. "I know. God, you guys made a mess of me," I said, laughing, and got up and jumped in the pool. The water was a shock to my system, but felt good, although their spooge didn't come off me as easily as I thought it would, and instead created that weird consistency that happens sometimes when cum mixes with water. Greg jumped in the pool, too, and then we both got out and grabbed the towels the guy had brought us earlier. He was just lying there, his cock slowly deflating, and watching us. "So when are you scheduled to do this yard again?" he asked. Greg and I smiled. "Next weekend...sir," Greg said, and we all laughed. We started to pull our shorts back on, and find where we'd put our shirts earlier, and the guy told us to feel free to come by anytime to use his pool. "And anything else you want to do." We were all kind of awkward, but were also sharing the joke of being awkward after what we'd just done. "You bet," I said. "You may get sick of us by the time your parents get home." "Don't worry, I'll let you know if I do," he said. We thanked him and left, and later that evening, in Greg's room, we sucked each other off again. In fact, I would be willing to bet we sucked each other off 30 or 40 more times that summer. I'm not kidding. We also traded blow jobs several times with the guy in the towel (I think I saw him wearing clothes only once or twice the entire time, until his parents returned), and hung out by his pool, always nude, having some brews, talking shit, jerking off and blowing each other. Later in August, another hunk of a lifeguard from his club started hanging out there with us as well, and the four of us went at it. It was probably illegal, with us being 16 and them over 21, but we didn't really think about it at the time. Maybe they did, I don't know. It all seems like some dream or something now, and I probably remember it with that gold filter teenage summers always seem like in memory, combined with the power of incredible sex. But it was a pretty incredible summer and seemed to alter everything else about my life. So much so that, while Greg and I kept working out and pumping up, we didn't even bother to go out for football after all. For our own, horny reasons, we went out for wrestling instead, and made the team. High school looked like it would be pretty good.

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